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WO2011033472A4 - Salts of sunitinib - Google Patents

Salts of sunitinib Download PDF

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Publication number
WO2011033472A4
WO2011033472A4 PCT/IB2010/054196 IB2010054196W WO2011033472A4 WO 2011033472 A4 WO2011033472 A4 WO 2011033472A4 IB 2010054196 W IB2010054196 W IB 2010054196W WO 2011033472 A4 WO2011033472 A4 WO 2011033472A4
Authority
WO
WIPO (PCT)
Prior art keywords
acid
sunitinib
salt
crystalline salt
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IB2010/054196
Other languages
French (fr)
Other versions
WO2011033472A1 (en
Inventor
Sudhir Singh Sanwal
Saridi Madhava Dileep Kumar
Swargam Sathyanarayana
Rajesh Kumar Thaper
Mohan Prasad
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ranbaxy Laboratories Ltd
Original Assignee
Ranbaxy Laboratories Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ranbaxy Laboratories Ltd filed Critical Ranbaxy Laboratories Ltd
Priority to CA2774634A priority Critical patent/CA2774634A1/en
Priority to IN3290DEN2012 priority patent/IN2012DN03290A/en
Priority to US13/496,559 priority patent/US20120220783A1/en
Priority to EP10760097.5A priority patent/EP2477978A1/en
Priority to AU2010296849A priority patent/AU2010296849A1/en
Publication of WO2011033472A1 publication Critical patent/WO2011033472A1/en
Publication of WO2011033472A4 publication Critical patent/WO2011033472A4/en
Anticipated expiration legal-status Critical
Priority to ZA2012/02565A priority patent/ZA201202565B/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to salts of sunitinib and their preparation.

Claims

AMENDED CLAIMS received by the International Bureau on 05 April 2011 (05.04.2011)
1. (Cancelled).
2. (Cancelled).
3. A salt of sunitinib with sulfuric acid, acetic acid, methanesulfonic acid,
ethanesulfonic acid or succinic acid.
4. A salt of sunitinib according to claim 3, wherein the salt of sunitinib with sulfuric acid, acetic acid, methanesulfonic acid, ethanesulfonic acid or succinic acid is in a solid form.
5. A salt of sunitinib according to claim 4, wherein the solid form comprises a
crystalline form.
6. A crystalline salt of sunitinib with citric acid.
7. A crystalline salt of sunitinib with citric acid having an XRPD pattern comprising any five of interplanar spacing (d) values selected from the group consisting of 15.72, 10.50, 9.39, 8.71, 7.19, 7.00, 6.50, 6.30, 5.70, 5.44, 5.38, 5.10, 4.72, 4.36, 4.21, 3.57, 3.50, 3.40, 3.28 and 3.14 (A).
8. A crystalline salt of sunitinib with p-toluenesulfonic acid.
9. A crystalline salt of sunitinib with p-toluenesulfonic acid having an XRPD pattern comprising any five of interplanar spacing (d) values selected from the group consisting of 18.51, 9.25, 8.05, 7.45, 7.04, 6.55, 6.17, 5.72, 5.38, 5.14, 4.96, 4.90, 4.84, 4.70, 4.59, 4.52, 4.33, 4.24, 4.15, 4.03, 3.91, 3.79, 3.70, 3.65, 3.54, 3.46, 3.36, 3.30, 3.20 and 3.11 (A).
10. A crystalline salt of sunitinib with sulfuric acid.
11. A crystalline salt of sunitinib with sulfuric acid having an XRPD pattern
comprising any five of interplanar spacing (d) values selected from the group consisting of 15.34, 13.23, 10.08, 9.53, 8.76, 7.66, 7.48, 7.04, 6.62, 6.54, 6.17, 6.06, 5.74, 5.49, 5.27, 5.10, 4.88, 4.82, 4.72, 4.50, 4.41, 4.31, 4.19, 4.07, 4.00, 3.97, 3.93, 3.83, 3.70, 3.65, 3.60, 3.54, 3.47, 3.44, 3.40, 3.27, 3.19 and 2.92 (A).
12. A crystalline salt of sunitinib with acetic acid.
13. A crystalline salt of sunitinib with acetic acid having an XRPD pattern comprising any five of interplanar spacing (d) values selected from the group consisting of 23.47, 14.60, 12.35, 11.68, 9.74, 8.06, 7.79, 6.70, 6.53, 6.09, 5.59, 5.41, 5.16, 4.94, 4.86, 4.68, 4.40, 4.15, 4.04, 4.00, 3.80, 3.65, 3.60, 3.54, 3.47, 3.41, 3.32, 3.28 and 3.04 (A).
14. A crystalline salt of sunitinib with methanesulfonic acid.
15. A crystalline salt of sunitinib with methanesulfonic acid having an XRPD pattern comprising any five of interplanar spacing (d) values selected from the group consisting of 15.18, 9.46, 8.58, 7.57, 7.03, 6.61, 6.36, 6.18, 5.78, 5.53, 5.28, 5.10, 5.04, 4.77, 4.72, 4.58, 4.34, 4.28, 4.21, 4.06, 3.91, 3.83, 3.78, 3.71, 3.68, 3.64, 3.58, 3.51, 3.43, 3.35, 3.26, 3.23, 3.15 and 3.00 (A).
16. A process for the preparation of a salt of sunitinib with sulfuric acid, acetic acid, methanesulfonic acid, ethanesulfonic acid or succinic acid-, wherein the process comprises treating sunitinib with sulfonic acid, acetic acid, methanesulfonic acid, ethanesulfonic acid or succinic acid.
17. A process according to the claim 16, wherein the treatment with the achiral acid is carried out in the presence of a solvent.
18. A process according to the claim 17, wherein the solvent comprises organic
solvents.
19. A process according to the claim 18, wherein the organic solvent comprises a
water-miscible organic solvent.
20. A process according to the claim 19, wherein the water-miscible organic solvent comprises a C1-3 alkanol.
21. (Cancelled).
PCT/IB2010/054196 2009-09-16 2010-09-16 Salts of sunitinib Ceased WO2011033472A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CA2774634A CA2774634A1 (en) 2009-09-16 2010-09-16 Salts of sunitinib
IN3290DEN2012 IN2012DN03290A (en) 2010-09-16 2010-09-16
US13/496,559 US20120220783A1 (en) 2009-09-16 2010-09-16 Salts of sunitinib
EP10760097.5A EP2477978A1 (en) 2009-09-16 2010-09-16 Salts of sunitinib
AU2010296849A AU2010296849A1 (en) 2009-09-16 2010-09-16 Salts of sunitinib
ZA2012/02565A ZA201202565B (en) 2009-09-16 2012-04-10 Salts of sunitinib

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1932DE2009 2009-09-16
IN1932/DEL/2009 2009-09-16

Publications (2)

Publication Number Publication Date
WO2011033472A1 WO2011033472A1 (en) 2011-03-24
WO2011033472A4 true WO2011033472A4 (en) 2011-05-26

Family

ID=43500174

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2010/054196 Ceased WO2011033472A1 (en) 2009-09-16 2010-09-16 Salts of sunitinib

Country Status (6)

Country Link
US (1) US20120220783A1 (en)
EP (1) EP2477978A1 (en)
AU (1) AU2010296849A1 (en)
CA (1) CA2774634A1 (en)
WO (1) WO2011033472A1 (en)
ZA (1) ZA201202565B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010011834A2 (en) 2008-07-24 2010-01-28 Teva Pharmaceutical Industries Ltd. Sunitinib and salts thereof and their polymorphs
EP2501694A1 (en) * 2009-11-19 2012-09-26 Ranbaxy Laboratories Limited Process for the preparation of crystalline form ii of l-malic acid salt of sunitinib
WO2013140232A1 (en) 2012-03-23 2013-09-26 Laurus Labs Private Limited An improved process for the preparation of sunitinib and its acid addition salts thereof
PL399027A1 (en) * 2012-04-27 2013-10-28 Instytut Farmaceutyczny Preparation method for high purity N- [2- (diethylamino) ethyl] -5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide and its use in the production of sunitinib
WO2014167436A2 (en) * 2013-04-10 2014-10-16 Shilpa Medicare Limited Sunitinib glucuronate salt & process for preparation thereof
CA2838585A1 (en) * 2013-10-18 2015-04-18 Hari Babu Matta An ascorbic acid salt of sunitinib
CN104744442B (en) * 2013-12-25 2019-05-28 江苏豪森药业集团有限公司 The preparation method of Sunitinib malate

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE369359T1 (en) 2000-02-15 2007-08-15 Sugen Inc PYRROLE SUBSTITUTED INDOLIN-2-ONE PROTEIN KINASE INHIBITORS
HRP20040112B1 (en) 2001-08-15 2012-03-31 Pharmacia & Upjohn Company Crystals including a malic acid salt of n-[2-(diethylamino)ethyl]-5-[(5-fluoro-2-oxo-3h-indole-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide, processes for its preparation and compositions thereof
EP2220072A2 (en) 2007-11-21 2010-08-25 Teva Pharmaceutical Industries Ltd. Polymorphs of sunitinib base and processes for preparation thereof
CN101983195A (en) 2008-02-21 2011-03-02 基因里克斯(英国)有限公司 Novel polymorphs and processes for their preparation
AR073807A1 (en) * 2008-10-10 2010-12-01 Medichem Sa PROCESS TO PREPARE SUNITINIB MALATE, SALT OF A WEAKER ACID THAN MALATE AS A INTERMEDIARY COMPOUND, AND PROCESS TO PREPARE SUCH INTERMEDIARY SALT.
EP2181991A1 (en) * 2008-10-28 2010-05-05 LEK Pharmaceuticals D.D. Novel salts of sunitinib

Also Published As

Publication number Publication date
CA2774634A1 (en) 2011-03-24
WO2011033472A1 (en) 2011-03-24
ZA201202565B (en) 2012-12-27
US20120220783A1 (en) 2012-08-30
AU2010296849A1 (en) 2012-05-03
EP2477978A1 (en) 2012-07-25

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